With Help From Dropbox, Mailbox's Reinvention Of The Inbox Has Only Just Begun

Gentry Underwood is thinking of new "snoozes" for his Mailbox app, just acquired by Dropbox

If you haven't tried it, the Mailbox app might make you scratch your head, as it did for Forbes.com contributor Adrian Kingsley-Hughes. "I like the idea of redefining how I handle my email," he writes, "but I need to be sure that the Mailbox way is better." Well, I have been using the app for the last month and, although far from perfect, I can unequivocally say that the Mailbox way is better for me. But there's more to the story than that.

As I wrote when the news came out that Mailbox had been acquired by Dropbox, what is interesting about the app is that it is "an email prosthetic designed to change your behavior." This is a profound thing, and hard to do, and goes some of the way towards explaining what Dropbox thinks it is buying beyond a pretty email client. And unlike my initial take on Mailbox, that it was a prime acquisition target for Google, or perhaps Apple, the Dropbox angle brought the parallels with Instagram to mind.

I took advantage of being in San Francisco for the HTML5 Developers Conference to go see Mailbox founder Gentry Underwood at his fancy new digs at Dropbox. I wanted to see how accurate my intuitions about that app were. What I found out was that the Instagram parallel is quite apt and that Underwood's reinvention of the inbox has only just begun.

A lot of the limitations that people have complained about, that it is only for iPhone, that it only works with Gmail, and that it doesn't support all of Gmail's features (i.e., filters) are completely intentional. Underwood was trying to make a minimum viable product (MVP) first for what is a maximally important part of many people's digital lives. Not only did he limit it to Gmail and iOS, but within iOS it is iPhone only, not iPad.

Limiting the scope in this way enabled Underwood and his team, who had previously made the social todo list app Orchestra, to look at the problem from a fresh perspective. "What is email about, what is the purpose of it? And what is checking mail on your phone, doing mail on your phone and processing it? What is that about?" Underwood asks. "And how are our needs different on these little computers in our pocket than when we just sat at a computer all day and logged on to some service and downloaded our mail?"

Underwood used his human centered design training from Stanford, followed by four-and-a-half years at IDEO to create "a more natural product that is more closely aligned with what people are actually trying to do." Six months ago, when Mailbox was still in development, Underwood wrote a guest post for TechCrunch about why "email is broken." A big part of it is that there is now too much of it, and our inbox needs to be as much about organization as communication.

In my use of the app so far, I have leaned on the ability to process (and mostly dismiss) messages quickly. And I file certain pressing things in folders. But as suggested by a 2011 IBM Research study, I rarely look at these filed messages. And since my filing is inconsistant, these systems don't really help more with the "refinding" of messages than a straight search of my full mail archive. In fact, because Mailbox does not yet search archived mail, only what is resident on your phone, I actually find myself using the Apple mail client as well for searching.

"Are you snoozing much?" asked Underwood, when I described to him how I was using the app. "Snoozes," as he has coined them, are methods for sending a message to the future where it will act as a reminder. This was not just a passing question by Underwood, but the subject of very pressing interest. "Snoozing" is, in fact, the secret sauce of Mailbox, and the most radical behavior change it is trying to promote.

The initial snoozes in this MVP have quite limited functionality, but he promises they will get better. Once there is a desktop client for Mailbox, he said, "you could snooze a message until you got back to your desk. Even though you had cleared out your mail, when you sat down at your computer three things would pop back in, that were really waiting for you to be in a place with a keyboard and a big screen."

All of the current snoozes are time-based. You can put something off till tomorrow, or next weekend, but these are really just laying the groundwork for geo-based alerts, for instance, where a message reappears in your inbox when you are at the store that an emailed coupon is from, or even a social-based reminder that would pop back in your inbox when you were meeting with a specific person. Email on your phone creates all of these new kinds of possibilities. "Since this thing is with you all the time, you can actually teach it to help you triage into time and space," said Underwood. "You route things to the future you, or to the you that's with someone else, or the you that's at home." Your email can respond to the conditional you.

Time turns out to be a pretty decent proxy for context or intent. It takes a bit more work, but not so much more, Underwood hopes, that it will stop people from adopting this new behavior. To me, having a desktop client would be really helpful, as would the ability to push messages from my phone to the desktop to deal with later. Being able to make desktop, Android, and iPad versions and fancier snoozes, Underwood told me, is the key reason they joined Dropbox. "Mobile email is a big market and there's a lot to do. At this point we're just struggling to meet the demand we already have."

Dropbox offers him resources and ready access to talent without having to do all the hiring himself. Beyond that, he sees Dropbox as "similarly focused on taking the pain out of work. Dropbox really exists to simplify your relationships to your stuff and make it accessible anywhere. Mailbox really exists to simplify your relationship to your email. So there's an alignment of philosophical values."

But what about integration with Dropbox, I asked? It turns out that even in terms of fairly obvious things like support for file attachments, there's no particular immediacy to tie the two services together. Integrations "are going to have to sit in a queue along with all of these other things we want to do around making mobile email better." Underwood said. "What's the most important one, that's going to take away the most pain or help us reach the most people? If that's not Dropbox integration, we won't do it. Amazingly, that's fine with them."

Dropbox does not seem to want to be in the email business, and Underwood himself is after transforming the inbox, not re-inventing the email systems that feed it. "I want to build a product that plays nice with the email that already exists, as opposed to replacing it," He said. "Gmail itself is a wonderful service and replicating it would be quite difficult. It's very smart. It's a great reliable platform that works. Google has made more leaps on making email great than any other company out there. I have tons of respect for them for doing that."

Underwood can imagine Twitter Direct Messages and Facebook messages going in the inbox. Or he imagines "an API that allows notifications from a ticketing system like Gira or Asana" to go into the inboxes of a company's employees. "If I like this inbox, it makes sense that I would want to feed more of my messages from other services into it." Underwood said, echoing Dropbox's approach to data. "Since what we're building is an inbox, it should be somewhat agnostic about where the information sources come from."

What will they do next? Underwood says it's his job "to listen to those things [that users want], lay them all out in terms of an opportunity space and pick the ones that seem like they're the most bang for the buck in terms of our own time and energy in terms of creating an even better product that reaches even more people." But there's a caution here as well. Email is so personal, remaking people's relationship to it is an awesome responsibility.

"That's actually what led to this crazy reservation system, was fear that if our system fell over it would be much ado about nothing, no matter how good the design was," Underwood said referring to the app's waiting list. Even the close friends and family they asked to test out the app would get very angry if something didn't work. "That was a very hard lesson," he said. "It reiterated what we knew in theory that email cannot go down, email needs to be as reliable as possible. If messages disappear your trust in the system will go away and we will lose you forever."

It turns out that, particularly with something as mission critical as email, designing how the data works is as important as making a beautiful interface. "It's unbelievable how fast we have scaled from a data perspective. Probably as fast or faster than any other company in the history of technology," Underwood said. "Of course, six months from now someone will be faster than us! A couple of weeks a go we were processing 60 million messages a day, it's probably more like 80 or 100 now. That's crazy in terms of a little team going from nothing to something like that in six weeks." He feels that even "from a design perspective, keeping the system up and running, keeping people's information secure, delivering emails reliably and quickly are as fundamental to this as the delight you feel through the UX. They're like two halves of the same point."

I was struck by how well thought-through the fallback systems for data are on an app that many have assumed is just a skin, just another pretty email client. The deeper point though, for me, was to understand that my own positive experience of the app was just a first step towards using email in a more organized and effective manner. The whole concept of "snoozing" messages is key to Underwood's vision of the product. Mailbox is not the only application to contain such a feature, but it does seem destined to occupy a very central place in what is becoming a very visible product.

But my own use of the snooze feature and Mailbox's implementation of it, have only just begun. Underwood has a very large loop that he is trying to close for users. We carry a tool around with us all day long that can help us use our time more efficiently, yet we prefer to fill up our interstitial time playing games and checking sports score. Quickly triaging messages on our phones is just the first, small part of this loop to close. In the larger vision of Mailbox, messages can be deployed in time, space and between people (as in Underwood's previous project, Orchestra) so that we are presented with the information we need to see when we are ready and able to deal with it—just-in-time messaging. And given the rise of machine intelligence and systems like GoogleNow, it is possible to imagine that we will eventually be able to train Mailbox to learn how to triage many of our messages in this way in an automated fashion.

I don't think it is a forgone conclusion, however, that users will fully embrace this larger vision, and I think Underwood fully realizes the difficulty of introducing new behaviors for familiar habits. From my own experience of how Maibox has changed the way I deal with my own email, I think it is likely that he can build larger and larger behavior changes into the product and over time, close that larger loop. "To build something that encourages a person down a path of behavior change—it doesn't get more difficult from a design perspective," Underwood acknowledged to me. And this is just what he is trying to do. For myself, I'm going to try "snoozing" more. Who knew that this might be the secret to waking up my inbox?